Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
  • A61K8/355—Quinones
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
  • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

• the present invention relates to the field of hair colorants. More specifically, the invention relates to semi-permanent hair coloring systems.
• the dye should provide a natural looking, durable and an even deposit of color on the hair. To achieve this, the dye must be able to penetrate the cuticle, and not wash out easily over a determined period of time. It is also preferred that the process that is used to achieve this end is not too harsh or damaging to the hair. Also, the color of the dyed hair should remain substantially reproducible between applications.
• the permanent dyes are as their name implies, more resistant to the fading process that is associated with semipermanent dyes.
• This type of hair coloring system is more complex however, because the dyeing process relies on the use of dye precursors. When on the hair, the dye precursors are converted to colored compounds that constitute the actual dyes that color the hair.
• the components of a permanent hair dye system are typically a primary intermediate, a coupler, and hydrogen peroxide. The oxidation of the primary intermediate, followed by coupling with the coupler molecule, typically produces chromophore. Although the color produced by this process is long-lasting and can achieve lightening of the hair due to bleaching of the hair shaft by hydrogen peroxide, it is not without its disadvantages.
• the present invention relates to a hair coloring system comprising a coloring-effective amount of a solubilized vat dye, and substantially no chemical oxidant, such as hydrogen peroxide.
• the coloring system can also confer color to hair in the absence of other coloring agents typically used for this purpose, for example, nitrophenols, aminophenols or phenylenediamines.
• the invention also provides a method for durably coloring the hair using solubilized vat dyes, in the absence of any added chemical oxidant.
• vat dyes The compounds known as vat dyes are well known. They have been used for thousands of years, examples being the naturally occurring indigo and tyrian purple. In modern times, dyes of this type have been made synthetically, and are widely used in the textile industry for dyeing of cloth, both natural and synthetic(see Joseph Rivlin, The Dyeing of Textile Fibers, Theory and Practice, Chapter 10, 1992, incorporated herein by reference). These dyes are aromatic compounds containing two or more carbonyl groups that are joined by conjugated double bonds. Unlike their permanent dye precursors, the vat dyes already contain their chromophore, and therefore do not require the presence of an oxidative agent to generate the chromophore on the hair.
• the soluble vat dyes are actually a group of dyes by themselves. They are vat dyes already in the reduced soluble form, and have the unique feature that they will not oxidize by merely exposing them to the air.
• the soluble vat dyes are esters of the leuco vat dyes. In presence of the acid and at the proper temperature, the ester will hydrolyze to yield the leuco acid of the vat dye, which can then be oxidized even by air, as are regular leuco vats, to its insoluble form. Solubilized vat dyes were originally used for textiles. This is because they offer many advantages:
• the solubilized vat dyes can be used in a significantly lowered pH and in diverse applications.
• Soluble vat dyes have previously been disclosed for use in dyeing hair, but only in combination with a standard peroxidation system(US Patent No. 5,364,415). However, to the best of Applicants' knowledge, solubilized vat dyes have never been used alone for the coloring of hair. Surprisingly, it was found that solubilized vat dyes out-perform other classes of dyes in the semi -permanent dye formula. For example, basic and direct dyes normally used in semi-permanent hair colors wash out after a few shampoos. Solubilized vat dyes, however, can last up to 45 shampoos.
• the solublized vat dye is easily penetrated into the hair and is then oxidized back to its insoluble form by simple exposure to the air. This oxidation thereby causes the dye to be retained by the hair and thus coloring the hair.
• solublized vat dyes of the invention can be any of the solublized vat dyes that are cosmetically acceptable.
• Vat dyes as well as solublized vat dyes encompass two chemical classes, namely the indigoids and the anthraquinone derivatives, with a preference for the anthraquinones because of their color fastness.
• useful solublized vat dyes include, but are not limited to, CI Solublized Vat Brown 5(CI 73411), CI Solublized Vat Black
• vat dyes are capable of being used alone, as the sole source of color in a dyeing composition, or in combination with another solublized vat dye.
• the amount of dye used is dependent upon the final shade desired, and is not particularly critical. However, the dyes are ordinarily used in an amount of about 0.5 to about 10% by weight of the composition, and preferably in a range of about 1 to about 5%.
• a useful additive to the dye solution is one or more antioxidants.
• the presence of the antioxidant(s) in the formulation aids in solubhzation of the dye, reducing precipitation of the dye, and ensuring that the dye is in optimum form for penetration and dyeing of the hair.
• useful antioxidants are erythorbic acid, sodium sulfite, sodium metabisulfite, and sodium hydrosulfite. When used, the antioxidant will be present in amount of from about 0.5- 5% by weight of the composition.
• a preferred combination is of sodium metabisulfite and erythorbic acid, particularly preferred in a ratio of about 2:1.
• an additional factor that may aid in performance is the use of an alcohol in the formulation, namely benzyl alcohol.
• the alcohol may constitute up to about 90%, or even more, of the composition, taking into account the other necessary components of the product.
• the amount of benzyl alcohol used will be about 0.5 to about 5% by weight.
• vat dyes are very versatile and applicable, it is possible to combine the vat dyes with other types of semi-permanent hair dyes.
• the semi-permanent dye systems of the present invention have many advantages over comparable existing dyes systems.
• the use of the solublized vat dyes avoids the use of harsh oxidants such as hydrogen peroxide, and thus reduces the possibility of hair damage due to the dyeing process so common with other dyes.
• the colors are also very bright, and easy to match because of its defined chromophore system.
• the dyes have a great affinity for the hair, and maintain an exceptional level of color-fastness even after many shampoos.
• the application of the dye system is also very simple, achievable in a simple rinse-off formula, with color development completed by air exposure, preferably coupled with a hair dryer at a moderate heat setting.
• the invention will be further understood by reference to the following non-limiting examples.
• the violet dye appeared to go into solution at constant rate, regardless of an antioxidant being added to the dye, or the pH of the solution. When sodium hydrosulfite was used, it did not go into aqueous solution when used in conjunction with erythorbic acid.
• the pH was adjusted to around 10 using various bases (ammonium hydroxide, AMP and NaOH). It is important to note that the solubilized vat dyes also work well in acidic conditions, and can therefore be used in a variety of formulas.
• L, a, and b values were determined with the use of a chromameter (Minolta) and graphed (figures 1 and 2).
• Swatch label “1” is a reference swatch in which it was dyed and then rinsed with tap water.
• Swatch "2” was dyed, rinsed and washed 5 times.
• the solution that the swatches were dyed with was 4% SVD (violet), 2% Sodium metabisulfite, 1% erythorbic acid and water.
• the solution for the above data consisted of 5% benzyl alcohol, 5% Solublized Vat Dye and water. The pH was adjusted to 10 using ammonium hydroxide.
• Solublized Vat dyes were incorporated into various formulas to determine applicability of the dyes. Some of the formulas are as follows:
• Sequence #1 ingredients were added and mixed until homogeneous. Sequence #2 ingredient was then added and mixed in thoroughly. At medium to high speed, Sequence #3 ingredients were mixed in. At medium mixing speed, Sequence #4 ingredients were added to the mixture and stirred until all lumps of powder dissolved. Finally, the pH was adjusted to 9 with Sequence #5.
• the product was applied to 4 yak, 4 natural white and 4 50% gray hair swatches, incubated for 10 minutes at 40° C and dried. One of each type of hair swatch was kept after dying process, one of each was rinsed with tap water after dyeing process, one of each was washed once with Aveda®Rosemary Mint Shampoo after dyeing process, and one of each was washed 5 times after dyeing process.
• Sequence #1 ingredients Place Sequence #2 ingredients into a 5-micron filter bag, placing the filter bag into the water mixture and circulate for 20 minutes. Add Sequence #3 ingredient with slower mixing to avoid foaming. Add slowly Sequence #4 to the mixture until homogeneous. Sequence #5 - #12 ingredients should be added in sequential order, insuring that each component is fully dissolved before adding the next one. Premix Sequence #13 ingredients in a separate container and add the mixture slowly to the main container and mix for 30 minutes. Finally, Sequence #14 ingredient can be added and mixed for 30 minutes.
• sequence #1 were combined at 60 degrees Celsius under moderate stirring for about 20 minutes or until gum and antioxidants were thoroughly dissolved. The temperature was then brought back down to STP for the remainder of the procedure. Slowly, sequence #2 ingredients were added and mixing continued, making sure the polymer was completely dispersed. Sequence #3 ingredients were then mixed in slowly until homogeneous. Sequence #4 ingredient (the vat dye) was then added until mixed thoroughly. The pH was adjusted to 5.5 ( ⁇ 0.2) with Sequence #5. Sequence #6 ingredient was slowly added and mixed until homogeneous. Sequence #7 was then mixed in slowly until batch was homogeneous. Indigo Hair Conditioner with Tea Tree Oil
• sequence #1 The ingredients of sequence #1 were combined at 60° Celsius under moderate stirring for about 20 minutes or until gum and antioxidants were thoroughly dissolved. The temperature was then raised to 78° Celsius. Sequence #2 was then added until a clear uniform solution was obtained. Sequence #3 was added, maintaining thorough mixing and temperature. In a separate mixing container, sequence #4 was mixed and heated to 72° Celsius. At proper temperature, Sequence #4 was added to the main container, maintaining temperature until emulsification was complete. The temperature was then cooled to 40° Celsius with slower mixing. At 40°C, Sequence #5 was added, cooling to 30° Celsius. At 30° Celsius, Sequence #6 was added and cooled to 25° Celsius.

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• 2001
  • 2001-05-29 US US09/867,278 patent/US6592632B2/en not_active Expired - Lifetime
• 2002
  • 2002-05-23 WO PCT/US2002/016803 patent/WO2002096383A1/en active IP Right Grant
  • 2002-05-23 JP JP2002592896A patent/JP4130590B2/ja not_active Expired - Fee Related
  • 2002-05-23 EP EP02726936A patent/EP1395236A4/en not_active Ceased
  • 2002-05-23 CA CA002448671A patent/CA2448671C/en not_active Expired - Fee Related

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